WO2011126063A1 - Composites de métal et composé utile pour leur préparation - Google Patents

Composites de métal et composé utile pour leur préparation Download PDF

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WO2011126063A1
WO2011126063A1 PCT/JP2011/058746 JP2011058746W WO2011126063A1 WO 2011126063 A1 WO2011126063 A1 WO 2011126063A1 JP 2011058746 W JP2011058746 W JP 2011058746W WO 2011126063 A1 WO2011126063 A1 WO 2011126063A1
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健太 田中
正洋 藤岡
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住友化学株式会社
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Priority to DE112011101194T priority Critical patent/DE112011101194T5/de
Priority to CN2011800159436A priority patent/CN102822230A/zh
Priority to US13/583,154 priority patent/US20130018155A1/en
Publication of WO2011126063A1 publication Critical patent/WO2011126063A1/fr

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D251/00—Heterocyclic compounds containing 1,3,5-triazine rings
    • C07D251/02—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings
    • C07D251/12—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
    • C07D251/14—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hydrogen or carbon atoms directly attached to at least one ring carbon atom
    • C07D251/16—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hydrogen or carbon atoms directly attached to at least one ring carbon atom to only one ring carbon atom
    • C07D251/20—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hydrogen or carbon atoms directly attached to at least one ring carbon atom to only one ring carbon atom with no nitrogen atoms directly attached to a ring carbon atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D251/00—Heterocyclic compounds containing 1,3,5-triazine rings
    • C07D251/02—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings
    • C07D251/12—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
    • C07D251/26—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with only hetero atoms directly attached to ring carbon atoms
    • C07D251/38—Sulfur atoms
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G61/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
    • C08G61/02—Macromolecular compounds containing only carbon atoms in the main chain of the macromolecule, e.g. polyxylylenes
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G61/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
    • C08G61/12—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule
    • C—CHEMISTRY; METALLURGY
    • C22—METALLURGY; FERROUS OR NON-FERROUS ALLOYS; TREATMENT OF ALLOYS OR NON-FERROUS METALS
    • C22C—ALLOYS
    • C22C32/00—Non-ferrous alloys containing at least 5% by weight but less than 50% by weight of oxides, carbides, borides, nitrides, silicides or other metal compounds, e.g. oxynitrides, sulfides, whether added as such or formed in situ
    • C22C32/0094—Non-ferrous alloys containing at least 5% by weight but less than 50% by weight of oxides, carbides, borides, nitrides, silicides or other metal compounds, e.g. oxynitrides, sulfides, whether added as such or formed in situ with organic materials as the main non-metallic constituent, e.g. resin
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B22—CASTING; POWDER METALLURGY
    • B22F—WORKING METALLIC POWDER; MANUFACTURE OF ARTICLES FROM METALLIC POWDER; MAKING METALLIC POWDER; APPARATUS OR DEVICES SPECIALLY ADAPTED FOR METALLIC POWDER
    • B22F2998/00—Supplementary information concerning processes or compositions relating to powder metallurgy
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G2261/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
    • C08G2261/10—Definition of the polymer structure
    • C08G2261/12—Copolymers
    • C08G2261/124—Copolymers alternating
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G2261/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
    • C08G2261/10—Definition of the polymer structure
    • C08G2261/14—Side-groups
    • C08G2261/141—Side-chains having aliphatic units
    • C08G2261/1412—Saturated aliphatic units
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G2261/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
    • C08G2261/10—Definition of the polymer structure
    • C08G2261/14—Side-groups
    • C08G2261/143—Side-chains containing nitrogen
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G2261/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
    • C08G2261/10—Definition of the polymer structure
    • C08G2261/14—Side-groups
    • C08G2261/149—Side-chains having heteroaromatic units
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G2261/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
    • C08G2261/30—Monomer units or repeat units incorporating structural elements in the main chain
    • C08G2261/31—Monomer units or repeat units incorporating structural elements in the main chain incorporating aromatic structural elements in the main chain
    • C08G2261/314—Condensed aromatic systems, e.g. perylene, anthracene or pyrene
    • C08G2261/3142—Condensed aromatic systems, e.g. perylene, anthracene or pyrene fluorene-based, e.g. fluorene, indenofluorene, or spirobifluorene
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G2261/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
    • C08G2261/30—Monomer units or repeat units incorporating structural elements in the main chain
    • C08G2261/32—Monomer units or repeat units incorporating structural elements in the main chain incorporating heteroaromatic structural elements in the main chain
    • C08G2261/322—Monomer units or repeat units incorporating structural elements in the main chain incorporating heteroaromatic structural elements in the main chain non-condensed
    • C08G2261/3223—Monomer units or repeat units incorporating structural elements in the main chain incorporating heteroaromatic structural elements in the main chain non-condensed containing one or more sulfur atoms as the only heteroatom, e.g. thiophene
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G2261/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
    • C08G2261/40—Polymerisation processes
    • C08G2261/41—Organometallic coupling reactions
    • C08G2261/411—Suzuki reactions

Definitions

  • the present invention relates to a metal complex and a compound useful for the preparation thereof.
  • Conjugated compounds with properties such as thermal conductivity, electrical conductivity, heat resistance, etc. are compounded with metals to compensate for each other's weaknesses and develop new functions. Is attracting attention as a new generation of materials. And in order to manufacture a metal composite, it is indispensable to adsorb
  • an object of this invention is to provide the compound which can adsorb
  • the present invention first provides a compound represented by the following formula (II-a).
  • Ar 2 represents an aromatic group which may have a substituent
  • R 2 represents a direct bond or an organic group which may have only an oxygen atom as a hetero atom.
  • E represents a hetero atom
  • R 3 represents a monovalent hydrocarbon group or a hydrogen atom
  • m t and n t each independently represents an integer of 1 or more
  • l t represents 1 to 3
  • a plurality of R 3 , E and l t may be the same or different from each other, and when there are a plurality of m t , they may be the same or different from each other.
  • X a and X b are each independently a halogen atom, a nitro group, —SO 3 Q (where Q represents a substituted or unsubstituted monovalent hydrocarbon group), —B (OQ 1 ) 2 (where, Q 1 is either a hydrogen atom or a monovalent hydrocarbon group, one of two Q 1 is bonded to Q 1 with .2 pieces to form a ring may being the same or different), -.
  • the present invention secondly provides a polymer compound having a structural unit represented by the following formula (Pa) and having a molecular weight of 5 ⁇ 10 2 to 1 ⁇ 10 7 .
  • Ar 2 represents an aromatic group which may have a substituent
  • R 2 represents a direct bond or an organic group which may have only an oxygen atom as a hetero atom.
  • E represents a hetero atom
  • R 3 represents a monovalent hydrocarbon group or a hydrogen atom
  • m t and n t each independently represents an integer of 1 or more
  • l t represents 1 to 3
  • a plurality of R 3 , E and l t may be the same or different from each other, and when there are a plurality of m t , they may be the same or different from each other. When there are a plurality of groups in parentheses to which m t and n t are attached, they may be the same as or different from each other.)
  • the present invention provides a metal composite obtained by bringing the polymer compound into contact with a film or plate metal, or a film or plate metal compound.
  • the present invention provides a metal composite obtained by contacting the polymer compound with metal nanoparticles having an aspect ratio of less than 1.5, or metal compound nanoparticles having an aspect ratio of less than 1.5.
  • the present invention provides an electronic device including the metal composite.
  • a compound capable of efficiently and strongly adsorbing a metal and a metal complex using the compound can be obtained.
  • the compound of the present invention is particularly useful as a raw material for advanced functional materials such as electronic composite materials.
  • adsorption means chemical adsorption or physical adsorption.
  • the compound of the present invention is a compound represented by the formula (II-a).
  • Ar 2 Examples of the aromatic group represented by the following include the remaining atomic groups obtained by removing two hydrogen atoms from the compounds represented by the following formulas (1) to (91). This aromatic group may have a substituent.
  • the formulas (1) to (12), (15) to (22), (24) to (31), Compounds represented by (37) to (40), (43) to (46), (49), (50), (59) to (76) are preferred, and the compounds represented by formulas (1) to (3), (8 ) To (10), (15) to (21), (24) to (31), (37), (39), (43) to (45), (49), (50), (59) to
  • the compound represented by (76) is more preferable, and the compounds represented by formulas (1) to (3), (8), (10), (15), (17), (21), (24), (30), ( 59), (60) and (61) are more preferred, and compounds represented by formulas (1) to (3), (8), (10) and (59) are particularly preferred.
  • the aromatic group represented by formula (1) may have, a halogen atom, a monovalent hydrocarbon group that may have a substituent, a mercapto group, a carbonyl mercapto group, a thiocarbonyl mercapto group, Hydrocarbon thio group optionally having substituent, hydrocarbon thiocarbonyl group optionally having substituent, hydrocarbon dithio group optionally having substituent, hydroxyl group, having substituent Optionally having a hydrocarbon oxy group, a carboxyl group, an aldehyde group, a hydrocarbon carbonyl group optionally having a substituent, a hydrocarbon oxycarbonyl group optionally having a substituent, having a substituent.
  • Optionally substituted hydrocarbon carbonyloxy group, cyano group, nitro group, amino group, optionally substituted hydrocarbon monosubstituted amino group, optionally substituted hydrocarbon disubstituted amino group, Hos Inomoto, which may have a substituent hydrocarbon monosubstituted phosphino group, which may have a substituent hydrocarbon-disubstituted phosphino group, wherein :-P ( O) (OH) 2 , A carbamoyl group, an optionally substituted hydrocarbon monosubstituted carbamoyl group, an optionally substituted hydrocarbon disubstituted carbamoyl group, the formula: —B (OH) 2 A group represented by: a boric acid ester residue, a sulfo group, a hydrocarbon sulfo group that may have a substituent, a hydrocarbon sulfonyl group that may have a substituent, and a substituent.
  • the aromatic group represented by may have only one kind of these substituents or may have two or more kinds. Moreover, when there are a plurality of substituents, they may be combined to form a ring.
  • the halogen atom as a substituent include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom, a fluorine atom, a chlorine atom, and a bromine atom are preferable, and a chlorine atom and a bromine atom are more preferable.
  • Examples of the monovalent hydrocarbon group which may have a substituent are a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, an isobutyl group, a t-butyl group, a pentyl group, and a hexyl group.
  • an aryl group is an alkyl group having 1 to 12 carbon atoms, more preferably an aryl group having 6 to 18 carbon atoms, an alkyl group having 1 to 6 carbon atoms, an aryl group having 6 to 12 carbon atoms particularly preferred.
  • a part or all (particularly 1 to 3, especially 1 or 2) of the hydrogen atoms constituting each group are the above-mentioned “monovalent optionally having substituent (s)”. It is a group that may be substituted with a “hydrocarbon group”.
  • the substituents are a hydrocarbon monosubstituted amino group, a hydrocarbon disubstituted amino group, a hydrocarbon monosubstituted phosphino group, a hydrocarbon disubstituted phosphino group, a hydrocarbon monosubstituted carbamoyl group, and a hydrocarbon disubstituted carbamoyl group.
  • 1 or 2 of hydrogen atoms constituting the group is a group which may be substituted with the above-mentioned “monovalent hydrocarbon group which may have a substituent”.
  • the boric acid ester residue as a substituent is, for example, a group represented by the following formula.
  • the monovalent heterocyclic group as a substituent is a remaining atomic group obtained by removing one hydrogen atom from a heterocyclic compound.
  • Heterocyclic compounds include pyridine, 1,2-diazine, 1,3-diazine, 1,4-diazine, 1,3,5-triazine, furan, pyrrole, thiophene, pyrazole, imidazole, oxazole, thiazole, oxa Monocyclic heterocyclic compounds such as diazole, thiadiazole, azadiazole; condensed polycyclic heterocyclic compounds in which two or more of the heterocyclic rings constituting the monocyclic heterocyclic compound are condensed; monocyclic heterocyclic Bridge two heterocyclic rings constituting a compound or one aromatic ring and one heterocyclic ring constituting a monocyclic heterocyclic compound with a divalent group such as a methylene group, an ethylene group or a carbonyl group.
  • Examples of the divalent hydrocarbon group represented by R ′ include a methylene group, an ethylene group, a 1,2-propylene group, a 1,3-propylene group, a 1,2-butylene group, a 1,3-butylene group, 1 Divalent saturated hydrocarbon groups having 1 to 50 carbon atoms such as 1,4-butylene group, 1,5-pentylene group, 1,6-hexylene group, 1,9-nonylene group, 1,12-dodecylene group; 2 carbon atoms such as ethenylene group, propenylene group, 3-butenylene group, 2-butenylene group, 2-pentenylene group, 2-hexenylene group, 2-nonenylene group, 2-dodecenylene group, etc., and ethynylene group To 50 divalent unsaturated hydrocarbon groups; cyclopropylene group, cyclobutylene group, cyclopentylene group, cyclohexylene group, a 1,2-
  • the hydrogen atom in these groups may be substituted with a substituent.
  • the hydrocarbon group having two or more ester bonds as a substituent is, for example, a group represented by the following formula. (Wherein R ′ and n have the same meaning as described above.)
  • the hydrocarbon group having two or more amide bonds as a substituent is, for example, a group represented by the following formula.
  • the metal cation represented by M is preferably a monovalent to trivalent ion, and Li, Na, K, Cs, Be, Mg, Ca, Ba, Ag, Al, Bi, Cu, Fe, Ga, Mn, Examples include ions of metals such as Pb, Sn, Ti, V, W, Y, Yb, Zn, and Zr.
  • the substituent includes carbon such as methyl group, ethyl group, propyl group, isopropyl group, butyl group, isobutyl group, and t-butyl group.
  • Examples thereof include alkyl groups having 1 to 10 atoms.
  • Examples of the monovalent hydrocarbon group represented by R include an alkyl group, a cycloalkyl group, an aryl group, and an aralkyl group.
  • the anion represented by M ′ is F ⁇ , Cl ⁇ , Br ⁇ , I ⁇ , OH ⁇ , ClO ⁇ , ClO 2 ⁇ , ClO 3 ⁇ , ClO 4 ⁇ , SCN ⁇ , CN ⁇ , NO 3 ⁇ , SO 4 2- , HSO 4 ⁇ , PO 4 3- , HPO 4 2- , H 2 PO 4 ⁇ , BF 4 ⁇ , PF 6 ⁇ , CH 3 SO 3 ⁇ , CF 3 SO 3 ⁇ , Tetrakis (imidazolyl) borate anion, 8-quinolinolato anion, 2-methyl-8-quinolinolato anion, 2-phenyl-8-quinolino
  • Examples of the monovalent heterocyclic group having a quaternized nitrogen atom as a substituent in the heterocyclic ring include groups represented by the following formulae. (Wherein R and M ′ have the same meaning as described above.)
  • R 2 As the organic group which may have only an oxygen atom as the hetero atom represented by the above, CH of a monovalent hydrocarbon group which may have the above substituent 2
  • An atomic group may be mentioned, and these groups may form a ring.
  • R 2 Preferably, the remaining atomic group obtained by removing part of the hydrogen atom from the optionally substituted alkyl group, or part of the hydrogen atom removed from the optionally substituted aryl group More preferably, the remaining atomic group obtained by removing a part of hydrogen atoms from an alkyl group having 1 to 12 carbon atoms, or the remaining atomic group obtained by removing a part of hydrogen atoms from a phenyl group. And more preferably a remaining atomic group obtained by removing a part of hydrogen atoms from an alkyl group having 1 to 6 carbon atoms, and a remaining atomic group obtained by removing a part of hydrogen atoms from a phenyl group.
  • examples of the hetero atom represented by E include an oxygen atom, a sulfur atom, a nitrogen atom, a phosphorus atom, a silicon atom, a selenium atom, and a tellurium atom, preferably an oxygen atom and a sulfur atom. And a nitrogen atom, more preferably an oxygen atom and a sulfur atom, and particularly preferably a sulfur atom.
  • E is an oxygen atom or a sulfur atom
  • R 3 When is a hydrogen atom, an isomerization reaction represented by the following reaction formula may occur. The compound produced by this isomerization reaction exhibits the same effect as the compound of the present invention.
  • E is a sulfur atom and R 3
  • R 3 When is a hydrogen atom, a structure of -EE is easily generated by a reaction between two molecules of -E-H. The compound produced by this reaction also exhibits the same effect as the compound of the present invention.
  • R 3 The monovalent hydrocarbon group represented by is the same as the monovalent hydrocarbon group which is explained and exemplified in the paragraph of the substituent and may have a substituent. Multiple R 3 May be the same or different from each other, and a plurality of R 3 They may form a ring.
  • X a And X b examples of the halogen atom represented by the formula include a fluorine atom, a chlorine atom, a bromine atom and an iodine atom, and a chlorine atom, a bromine atom and an iodine atom are preferable.
  • the substituted or unsubstituted monovalent hydrocarbon group represented by Q is the same as the monovalent hydrocarbon group which may have a substituent described and exemplified in the paragraph of the substituent. is there.
  • a fluorine atom is mentioned as a substituent.
  • X a And X b -SO represented by 3
  • Q include a methanesulfonate group, a benzenesulfonate group, a p-toluenesulfonate group, and a trifluoromethanesulfonate group.
  • the monovalent hydrocarbon group represented by the above examples include monovalent hydrocarbon groups which may be substituted as described and exemplified in the above-mentioned substituent group, but an alkyl group is preferable, and methyl Group, ethyl group, propyl group, isopropyl group, butyl group, isobutyl group, pentyl group, hexyl group and nonyl group are more preferable, and methyl group, ethyl group, propyl group, butyl group, pentyl group and hexyl group are more preferable.
  • Examples of the monovalent hydrocarbon group represented by the above include monovalent hydrocarbon groups which may be substituted as described and exemplified in the above-mentioned substituent group, but an alkyl group is preferable, and methyl Group, ethyl group, propyl group, isopropyl group, butyl group, isobutyl group, pentyl group, hexyl group and nonyl group are more preferable, and methyl group, ethyl group, propyl group, butyl group, pentyl group and hexyl group are more preferable.
  • X a And X b Is preferably a halogen atom, -SO 3 Q, -B (OQ 1 ) 2 , -B (OQ 01 ) 3 ⁇ M a More preferably, a chlorine atom, a bromine atom, an iodine atom, -SO 3 Q is more preferably a chlorine atom, bromine atom, iodine atom or trifluoromethanesulfonate group, particularly preferably a chlorine atom, bromine atom or iodine atom, particularly preferably a bromine atom.
  • l t Is an integer of 1 to 3.
  • R directly connected to E when E is a silicon atom 3 L representing the number of t R is directly connected to E when E is a nitrogen atom or a phosphorus atom 3 L representing the number of t Is 2, and when E is an oxygen atom, sulfur atom, selenium atom or tellurium atom, R directly connected to E 3 L representing the number of t Is 1.
  • a compound represented by the following formula (II-a) is preferable, and a compound represented by the following formula (II-c) is more preferable.
  • E 0 represents a sulfur atom or an oxygen atom.
  • R 02 When there are a plurality of these, they may be the same as or different from each other.
  • R 3 , X a And X b Has the same meaning as described above.
  • n t When there are a plurality of groups in parentheses marked with, they may be the same as or different from each other. ) (Wherein R 3 , R 4 And E 0 Has the same meaning as described above.
  • X aa And X bb Each independently represents a chlorine atom, a bromine atom or an iodine atom.
  • R in the formula (II-b) 02 The divalent hydrocarbon group represented by is the same as the divalent hydrocarbon group described and exemplified in the section of the divalent hydrocarbon group represented by R ′, but a phenylene group is preferable.
  • Examples of the halogen atom represented by the formula include a fluorine atom, a chlorine atom, a bromine atom and an iodine atom, and a chlorine atom, a bromine atom and an iodine atom are preferable.
  • the monovalent hydrocarbon group represented by is the same as the monovalent hydrocarbon group which may be substituted as described and exemplified in the paragraph of the substituent.
  • Examples of the compound of the present invention include compounds represented by the following formulas (F-1) to (F-29), and are represented by the following formulas (F-1) to (F-12). Compounds are preferred.
  • ⁇ Production method of compound> The compound of the present invention may be synthesized by any method, but an example of the synthesis method will be described below (Scheme A). This scheme A is X a And X b Applicable when is a halogen atom.
  • Another example of the method for synthesizing the compound of the present invention includes a method of reacting a compound represented by the following formula (II-t) with a compound represented by the following formula (II-u). (Wherein R 2 , R 3 , E, l t And m t Has the same meaning as described above.
  • X c Is a halogen atom, a nitro group, -SO 3 Q, -B (OQ 1 ) 2 , -B (OQ 01 ) 3 ⁇ M a , -Si (Q 2 ) 3 Or -Sn (Q 3 ) 3 Represents.
  • m t When there are a plurality of groups in parentheses marked with, they may be the same as or different from each other. ) (Wherein Ar 2 , X a , X b And n t Has the same meaning as described above.
  • X d Is a halogen atom, a nitro group, -SO 3 Q, -B (OQ 1 ) 2 , -B (OQ 01 ) 3 ⁇ M a , -Si (Q 2 ) 3 Or -Sn (Q 3 ) 3 Represents. ) X in the formula (II-t) c And X in the formula (II-u) d When is a halogen atom, Kumada-Tamao coupling can be used.
  • the compound represented by the formula (II-t) or the compound represented by the formula (II-u) in advance with magnesium or with alkylmagnesium chloride or the like, X c Or X d -MgX c , -MgX d Or -MgCl followed by a nickel catalyst (eg, NiCl 2 (Dppe) 2 ) Or palladium catalyst (eg, Pd (PPh 3 ) 4 In the presence of), the compound represented by the formula (II-a) can be obtained by reacting with the other.
  • a nickel catalyst eg, NiCl 2 (Dppe) 2
  • palladium catalyst eg, Pd (PPh 3 ) 4
  • the compound represented by the formula (II-a) can be obtained by reacting with the other.
  • Yamamoto coupling can also be used. That is, the compound represented by the formula (II-t) and the compound represented by the formula (II-u) are converted into a nickel catalyst (for example, bis (1,5-cyclooctadiene) nickel (0)
  • the compound represented by the formula (II-a) can be obtained by coupling in the presence of ().
  • X in the formula (II-t) c X in the formula (II-u) d One is a halogen atom and the other is -B (OQ 1 ) 2 Or -B (OQ 01 ) 3 ⁇ M a
  • a Suzuki-Miyaura coupling can be used. That is, the compound represented by the formula (II-t) and the compound represented by the formula (II-u) are converted into a base and a palladium catalyst (for example, Pd (PPh 3 ) 4
  • the compound represented by the formula (II-a) can be obtained by coupling in the presence of ().
  • the compound represented by the formula (II-t) and the compound represented by the formula (II-u) may be converted into an Ullmann reaction, a Gracer reaction, a Mizorogi-Heck reaction, a Negishi coupling, a Still cup.
  • the compound represented by the formula (II-a) can be obtained by ring, Sonogashira coupling, Buchwald-Hartwig reaction, or the like.
  • the polymer compound of the present invention has a structural unit represented by the formula (Pa) and has a molecular weight of 5 ⁇ 10. 2 ⁇ 1 ⁇ 10 7 It is a high molecular compound.
  • the polymer compound of the present invention is preferably a conjugated polymer compound because the charge easily moves in the molecule. Since the molecular weight of the polymer compound of the present invention is excellent in electrical conductivity and coatability, 1 ⁇ 10 3 ⁇ 2 ⁇ 10 6 Is preferred 2 ⁇ 10 3 ⁇ 1 ⁇ 10 6 Is more preferable, 2 ⁇ 10 3 ⁇ 5 ⁇ 10 5 Is more preferable. The molecular weight of the resulting polymer compound may not be uniform, and it may be difficult to accurately measure the molecular weight.
  • the number average molecular weight or the weight average molecular weight is obtained from the molecular weight distribution converted into a standard polymer compound such as polystyrene, and used as the molecular weight of the conjugated compound.
  • Ar in the formula (II-a) 2 , R 2 , E, R 3 , M t , N t And l t It is the same as described and exemplified as.
  • Examples of the structural unit represented by the formula (Pa) include X of the compounds represented by the formulas (F-1) to (F-28).
  • the structural unit represented by the formula (P-a) has excellent conductivity, HOMO energy level, LUMO energy level, and ease of synthesis. Therefore, the structural unit represented by the following formula (P-b)
  • R 3 And E 0 May be the same as or different from each other.
  • R 02 When there are a plurality of these, they may be the same as or different from each other.
  • n t When there are a plurality of groups in parentheses marked with, they may be the same as or different from each other.
  • R in the above formula (Pb) 02 Is preferably a phenylene group.
  • E in the formula (Pc) 0 , R 3 And R 4 Is E in the formula (II-c) 0 , R 3 And R 4 It is the same as described and exemplified as.
  • the polymer compound of the present invention may be a homopolymer composed only of the structural units described above, or may be a copolymer including other structural units.
  • Examples of other structural units include a structural unit composed of a dioctyl fluorenediyl group, a structural unit composed of a bithiophenediyl group, and the like, -Ar 2 -The structural unit represented by-(Note that this structural unit is different from the structural unit represented by the formula (P-a)).
  • the polymer compound of the present invention is a copolymer, the adsorption to the metal nanoparticles or metal compound nanoparticles becomes stronger and the solubility in a solvent is improved.
  • the number of structural units represented by the formula (Pa) contained is preferably 1 to 2000, more preferably 1 to 1000, still more preferably 1 to 200, particularly preferably 1 to 50, 1 to 20 is particularly preferable.
  • the polymer compound of the present invention may be synthesized by any method. As an example of the synthesis method, a method using the compound of the present invention will be described below.
  • the polymer compound of the present invention may be reacted, for example, using the compound of the present invention alone, but the compound of the present invention, the compound represented by the following formula (Va) and / or the following formula (You may make it react together with the compound represented by Vb).
  • Va the compound represented by the following formula
  • Each of these compounds may be used alone or in combination of two or more. (Where X a , X b And Ar 2 Has the same meaning as described above. ) (Where X a And Ar 2 Has the same meaning as described above.
  • the resulting polymer compound is a polymer compound composed only of the structural unit represented by the formula (Pa).
  • the compound of the present invention is reacted in combination with the compound represented by the formula (Va) and / or the compound represented by the formula (Vb)
  • the resulting polymer compound is It is a high molecular compound containing the structural unit represented by a following formula (PVa), and / or the group represented by a following formula (PVb).
  • the resulting polymer compound is Ar 2
  • the group represented by the formula is likely to have a linear structure in which the chain is continuous, and the group represented by the formula (PVb) is included as a terminal thereof.
  • the compound represented by the formula (Va) and / or the compound of the present invention may further be -X.
  • the resulting polymer compound has a dendritic or network structure.
  • X of the compound of the present invention a And X b When is a halogen atom, Kumada-Tamao coupling can be used.
  • X of the compound of the present invention a And X b
  • Yamamoto coupling can also be used. That is, the polymer compound of the present invention can be obtained by coupling in which the compound of the present invention is reacted in the presence of a nickel catalyst (for example, bis (1,5-cyclooctadiene) nickel (0)).
  • a nickel catalyst for example, bis (1,5-cyclooctadiene
  • X of these compounds a And X b Is preferably a halogen atom.
  • X of the compound of the present invention a And X b
  • One of the is a halogen atom, (1) The other is -B (OQ 1 ) 2 Or -B (OQ 01 ) 3 ⁇ M a If it is, (2) X of the compound of the present invention a And X b Is a halogen atom, and X of the compound represented by the above formula (Va) is present a And X b And X of the compound represented by the formula (Vb) a -B (OQ 1 ) 2 Or -B (OQ 01 ) 3 ⁇ M a Or (3) X of the compound of the present invention a And X b -B (OQ 1 ) 2 Or -B (OQ 01 ) 3 ⁇ M a And X of the compound represented by the above formula (Va) a And X b And / or X of the compound represented by the formula (Vb) a And X b When both are halogen
  • the compound of the present invention is converted to a base and a palladium catalyst (eg, Pd (PPh 3 ) 4
  • the polymer compound of the present invention can be obtained by the reaction in the presence of ().
  • the polymer compound of the present invention can be produced by subjecting the compound of the present invention to Ullmann reaction, Gracer reaction, Mizorogi-Heck reaction, Negishi coupling, Stille coupling, Sonogashira coupling, Buchwald-Hartwig reaction, etc. Can be obtained.
  • the polymer compound of the present invention is represented by R in the formula (Pa). 3 Is preferably a hydrogen atom because it can be more efficiently and more strongly adsorbed to metal nanoparticles or metal compound nanoparticles.
  • the compound of the present invention is R 3
  • the coupling reaction or the like may not easily proceed.
  • R 3 After synthesizing a polymer compound using the compound of the present invention in which is not a hydrogen atom, a carboxylic acid such as aluminum chloride or formic acid, a sulfonic acid such as trifluoromethanesulfonic acid, or the like is used.
  • R 3 It is preferable to carry out a reaction for converting to a hydrogen atom.
  • the metal composite of the present invention includes the polymer compound of the present invention and a film-like or plate-like metal, or a film-like or plate-like metal compound, or metal nanoparticles or an aspect having an aspect ratio of less than 1.5. It is a metal composite obtained by contacting metal compound nanoparticles having a ratio of less than 1.5.
  • the thickness of the film-like or plate-like metal, or the film-like or plate-like metal composite is usually 0.01 nm to 10 cm, preferably 0.01 nm to 0.5 cm, and preferably 0.01 nm to 200 ⁇ m. Is more preferable, and 0.01 nm to 20 ⁇ m is even more preferable.
  • Examples of the metal or metal constituting the metal compound include aluminum, scandium, titanium, vanadium, chromium, manganese, iron, cobalt, nickel, copper, zinc, gallium, germanium, yttrium, zirconium, niobium, molybdenum, ruthenium, Rhodium, palladium, silver, cadmium, indium, tin, antimony, lanthanum, cerium, europium, hafnium, tantalum, tungsten, rhenium, osmium, iridium, platinum, gold, mercury, thallium, lead, bismuth, aluminum, titanium , Vanadium, chromium, manganese, iron, cobalt, nickel, copper, zinc, gallium, germanium, yttrium, zirconium, molybdenum, ruthenium, rhodium, palladium, silver, indium, tin, Timon, lanthanum, cerium, tantalum,
  • metal compound examples include alloys, metal oxides, composite oxides, metal nitrides, metal sulfides, and metal salts, and alloys, metal oxides, composite oxides, and metal sulfides are preferable.
  • Metal compounds include indium tin oxide (ITO), indium zinc oxide (IZO), molybdenum oxide, aluminum oxide, titanium oxide, zinc oxide, copper oxide, copper dioxide, magnesium oxide, yttrium oxide, tungsten oxide (VI) , Silicon oxide, tin (IV) oxide, nickel tungsten, cerium oxide, manganese oxide, tin sulfide, cobalt oxide, holmium oxide, cobalt tetroxide, iron tetroxide, cobalt aluminate (CoAl 2 O 4 ), Spinel (Al 2 O 3 Indium tin oxide, indium zinc oxide, molybdenum oxide, aluminum oxide, titanium oxide, zinc oxide, copper oxide, copper dioxide, magnesium oxide, yttrium oxide, tungs
  • the film-like or plate-like metal or film-like or plate-like metal oxide is formed by casting, rolling, chamfering, polishing, etc., vacuum deposition such as vapor deposition, sputtering, ion plating, electroplating, Although it can be produced by plating treatment such as anodic oxidation, electroless plating, chemical plating, etc., application of a particle dispersion, etc., those produced by rolling, vapor deposition, sputtering, or ion plating are preferred.
  • the metal nanoparticles and metal composite nanoparticles usually have a longest axis length of 10 ⁇ m or less, preferably 0.1 nm to 1 ⁇ m, more preferably 1 nm to 500 nm.
  • the metal nanoparticles and metal compound nanoparticles have an aspect ratio (that is, the longest diameter / the shortest diameter, which is an average value when the aspect ratio is distributed) of less than 1.5.
  • the ratio is preferably 1.4 or less, more preferably 1.3 or less, still more preferably 1.2 or less, and particularly preferably 1.1 or less.
  • the metal nanoparticles may be the metal itself, or other metal adsorbed on the metal.
  • the metal compound nanoparticles may be the metal compound itself or those obtained by adsorbing other substances on the metal compound.
  • the contact includes (1) a method of attaching the polymer compound of the present invention to a film-like or plate-like metal, or a film-like or plate-like metal compound, and (2) a polymer compound of the present invention to a film-like or A method of applying to a plate-like metal, or a film-like or plate-like metal compound, (3) A method of stirring or kneading the polymer compound of the present invention and metal nanoparticles or metal compound nanoparticles. Can do.
  • a solvent is preferably interposed.
  • other components may coexist in the system, or ultrasonic waves may be applied.
  • a solution containing 0.0001 to 50% by weight of the polymer compound of the present invention is prepared and applied to a film-like or plate-like metal, or a film-like or plate-like metal compound. It is preferable.
  • the solvent when a solvent is interposed at the time of contact, the solvent can dissolve the polymer compound of the present invention and does not dissolve the metal nanoparticles or metal compound nanoparticles. Is usually used.
  • This solvent includes methanol, ethanol, benzyl alcohol, acetone, methyl ethyl ketone, dimethylformamide, dimethyl sulfoxide, ethyl acetate, toluene, xylene, orthodichlorobenzene, chloroform, tetrahydrofuran, hexane, benzene, diethyl ether, acetonitrile, acetic acid, Examples include water, propanol, butanol, and N-methylpyrrolidone.
  • this solvent may be used individually by 1 type, or may use 2 or more types together.
  • the temperature for stirring and kneading is preferably -70 ° C to 200 ° C, more preferably -10 ° C to 120 ° C, still more preferably 0 ° C to 100 ° C, and particularly preferably 20 ° C. ° C to 70 ° C.
  • the stirring and kneading time is preferably 0.01 seconds to 1000 minutes, more preferably 0.1 seconds to 900 minutes, and further preferably 1 second to 500 minutes.
  • a step of purifying the obtained complex (hereinafter referred to as “purification step”) may be performed.
  • the solvent can be removed by heating and drying the resulting composite.
  • the excess can be obtained by spraying a solvent capable of dissolving the polymer compound or immersing the obtained complex in the solvent.
  • the high molecular compound can be removed.
  • excess polymer compound is removed by ultrasonic dispersion, centrifugation, supernatant removal, redispersion, dialysis, filtration, washing, heating, drying, etc. can do.
  • an electronic device including the metal composite of the present invention that is, an electronic device in which the polymer compound of the present invention and a metal or a metal compound are stacked in layers can easily transfer charges between the layers.
  • the flowing current is increased.
  • the electronic device of the present invention include light emitting devices such as organic EL devices, photoelectric conversion devices such as transistors and solar cells.
  • the polymer compound J has two types of repeating units represented by the following formula. Structural unit represented by the following formula in polymer compound J: Was 4.4 mol%. Moreover, the number average molecular weight of polystyrene conversion of the high molecular compound J was 6.7 * 10 ⁇ 3 >, and the weight average molecular weight of polystyrene conversion was 1.3 * 10 ⁇ 4 >.
  • a 50 ml flask was charged with 485 mg of polymer compound J and 31.5 ml of toluene and stirred at room temperature. Subsequently, after adding aluminum chloride, it stirred at 115 degreeC for 1 hour.
  • the solid is considered to be a polymer compound P-1 (polymer) having two types of repeating units represented by the following formula.
  • the number average molecular weight in terms of polystyrene of the polymer compound P-1 was 6.6 ⁇ 10 3
  • the weight average molecular weight in terms of polystyrene was 1.6 ⁇ 10 4 .
  • the polymer compound G has two types of repeating units represented by the following formula.
  • the number average molecular weight of polystyrene conversion of the high molecular compound G was 7.9 * 10 ⁇ 3 >, and the weight average molecular weight of polystyrene conversion was 1.9 * 10 ⁇ 4 >.
  • a 50 ml flask was charged with 80 mg of polymer compound G and 20 ml of toluene, and stirred for 10 minutes at room temperature. Subsequently, after adding aluminum chloride, it stirred for further 1 hour. The organic layer in the reaction vessel was dropped into 500 ml of methanol to deposit a precipitate. The precipitate was filtered and dried to obtain 40 mg of a solid.
  • polymer compound K is represented by the following formula. (In the formula, n and m are numbers representing the number of repeating units.
  • N m is 7: 1 when estimated from the charging ratio.
  • N m is 7: 1 when estimated from the charging ratio.
  • the solid is considered to be a polymer compound P-3 (polymer) represented by the following formula. (In the formula, n and m are numbers representing the number of repeating units.
  • N m is 7: 1 when estimated from the charging ratio.
  • the number average molecular weight in terms of polystyrene of the polymer compound P-3 was 4.3 ⁇ 10 3 , and the weight average molecular weight in terms of polystyrene was 1.5 ⁇ 10 4 .
  • 6.7 mg of the polymer compound P-1 was dissolved in 3 mL of toluene.
  • Example 7 Take 7 mg of silver nanoparticles (nano powder, particle size: ⁇ 100 nm, 99.5% trace metals base, manufactured by Aldrich), add to 1.5 mL of toluene, put the whole container in an ultrasonic cleaner and ultrasonicate the silver particles. Diffused. At this time, the liquid was cloudy in gray for a while, but after 1 hour, silver nanoparticles were precipitated and the supernatant became transparent. After once again diffusing the silver particles with ultrasonic waves, 2 mg of the polymer compound P-1 was added and stirred, the resulting dispersion was still turbid even after 1 hour and the silver particles were dispersed.
  • Hexane is distilled off from an hexane solution of silver nanoparticles surface-modified with dodecanethiol (particle size (DLS): 5-15 nm, 0.25% (w / v) hexane solution, manufactured by Aldrich) with an evaporator (here The weight of silver nanoparticles was 8.6 mg), and 2.2 g of toluene was added to prepare a toluene solution of silver nanoparticles. 1.32 g was taken from the toluene solution of silver nanoparticles, 1.29 g was taken from the polymer compound P-3 toluene solution, and both were mixed. The obtained mixed solution was transparent and uniform, and no precipitate was formed.
  • DLS particle size
  • PHS particle size
  • the dodecanethiol on the surface of the silver nanoparticles was replaced by the polymer compound P-3, and methanol.
  • the silver nanoparticles are precipitated together with the polymer compound P-3, and no silver nanoparticles are present in the liquid.
  • This precipitate is a complex of the polymer compound P-3 and silver nanoparticles.
  • This precipitate was separated from the methanol solution using a centrifuge, dried, and measured for 1 H-NMR spectrum (in deuterated chloroform, TMS standard), there was no signal that could be attributed to dodecanethiol.

Abstract

L'invention concerne un composé de haut poids moléculaire ayant un poids moléculaire de 5×102 à 1×107, qui comprend des motifs structuraux représentés par la formule générale (P-a). Dans la formule générale (P-a), Ar2 représente un groupe aromatique éventuellement substitué ; R2 représente une liaison directe ou un groupe organique dans lequel le seul hétéroatome qui peut être contenu est un atome d'oxygène ; E représente un hétéroatome ; R3 représente un groupe hydrocarboné monovalent ou un atome d'hydrogène ; mt et nt représentent indépendamment chacun un nombre entier supérieur ou égal à 1 ; lt est un nombre entier de 1 à 3 ; les multiples R3, E et lt peuvent être chacun identiques ou différents les uns des autres ; lorsque de multiples mt sont présents, les mt peuvent être identiques ou différents les uns des autres ; et lorsque de multiples groupes dans les parenthèses avec mt ou nt sont présents, les multiples groupes peuvent être identiques ou différents les uns des autres.
PCT/JP2011/058746 2010-04-05 2011-03-31 Composites de métal et composé utile pour leur préparation WO2011126063A1 (fr)

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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2012133465A1 (fr) * 2011-03-28 2012-10-04 住友化学株式会社 Dispositif électronique, composé polymère, composé organique et procédé de production du composé polymère

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2016104359A1 (fr) * 2014-12-26 2016-06-30 昭和電工株式会社 Procédé de production de nanofils d'argent, nanofils d'argent obtenus à l'aide dudit procédé, et encre contenant lesdits nanofils d'argent
KR101850243B1 (ko) * 2016-03-28 2018-04-23 주식회사 엘지화학 화합물 및 이를 포함하는 유기 전자 소자

Citations (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH09302073A (ja) * 1996-05-09 1997-11-25 Agency Of Ind Science & Technol 多分岐重合体およびその製造方法
JP2001167885A (ja) * 1999-09-29 2001-06-22 Konica Corp 有機エレクトロルミネッセンス素子
JP2006225428A (ja) * 2005-02-15 2006-08-31 Tokyo Institute Of Technology １，３，５−トリアジン環を有する共重合体、その製造法およびその使用
WO2009124627A1 (fr) * 2008-04-07 2009-10-15 Merck Patent Gmbh Dérivés du fluor pour dispositifs électroluminescents organiques
WO2010041559A1 (fr) * 2008-10-06 2010-04-15 住友化学株式会社 Composé polymère contenant une structure hétérocyclique contenant de l'azote et composition, solution, film mince et élément électroluminescent polymère contenant chacun celui-ci
WO2010087510A1 (fr) * 2009-01-29 2010-08-05 住友化学株式会社 Composé de masse moléculaire élevée et élément émettant de la lumière l'utilisant
WO2010117075A1 (fr) * 2009-04-10 2010-10-14 住友化学株式会社 Complexe métallique et composition le contenant
WO2010131930A2 (fr) * 2009-05-15 2010-11-18 제일모직 주식회사 Composé pour dispositif photoélectrique organique et dispositif photoélectrique organique comprenant ce composé
WO2010136109A1 (fr) * 2009-05-29 2010-12-02 Merck Patent Gmbh Matériaux pour dispositifs électroluminescents organiques

Family Cites Families (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP2399970A3 (fr) * 2002-09-05 2012-04-18 Nanosys, Inc. Nano-composites
US20040124504A1 (en) * 2002-09-24 2004-07-01 Che-Hsiung Hsu Electrically conducting organic polymer/nanoparticle composites and methods for use thereof
US7317047B2 (en) * 2002-09-24 2008-01-08 E.I. Du Pont De Nemours And Company Electrically conducting organic polymer/nanoparticle composites and methods for use thereof
DE10356099A1 (de) * 2003-11-27 2005-07-07 Covion Organic Semiconductors Gmbh Organisches Elektrolumineszenzelement
US7455886B2 (en) * 2005-08-22 2008-11-25 Eastman Kodak Company Nanocomposite materials and an in-situ method of making such materials
JP5353186B2 (ja) 2007-11-30 2013-11-27 住友化学株式会社 アミン系高分子化合物及びそれを用いた発光素子
CN102132438A (zh) * 2008-07-30 2011-07-20 住友化学株式会社 层叠结构体、其制造方法和含有其的电子元件
KR20120102489A (ko) * 2009-04-10 2012-09-18 스미또모 가가꾸 가부시키가이샤 금속 복합체 및 그의 조성물

Patent Citations (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH09302073A (ja) * 1996-05-09 1997-11-25 Agency Of Ind Science & Technol 多分岐重合体およびその製造方法
JP2001167885A (ja) * 1999-09-29 2001-06-22 Konica Corp 有機エレクトロルミネッセンス素子
JP2006225428A (ja) * 2005-02-15 2006-08-31 Tokyo Institute Of Technology １，３，５−トリアジン環を有する共重合体、その製造法およびその使用
WO2009124627A1 (fr) * 2008-04-07 2009-10-15 Merck Patent Gmbh Dérivés du fluor pour dispositifs électroluminescents organiques
WO2010041559A1 (fr) * 2008-10-06 2010-04-15 住友化学株式会社 Composé polymère contenant une structure hétérocyclique contenant de l'azote et composition, solution, film mince et élément électroluminescent polymère contenant chacun celui-ci
WO2010087510A1 (fr) * 2009-01-29 2010-08-05 住友化学株式会社 Composé de masse moléculaire élevée et élément émettant de la lumière l'utilisant
WO2010117075A1 (fr) * 2009-04-10 2010-10-14 住友化学株式会社 Complexe métallique et composition le contenant
WO2010131930A2 (fr) * 2009-05-15 2010-11-18 제일모직 주식회사 Composé pour dispositif photoélectrique organique et dispositif photoélectrique organique comprenant ce composé
WO2010136109A1 (fr) * 2009-05-29 2010-12-02 Merck Patent Gmbh Matériaux pour dispositifs électroluminescents organiques

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2012133465A1 (fr) * 2011-03-28 2012-10-04 住友化学株式会社 Dispositif électronique, composé polymère, composé organique et procédé de production du composé polymère
US9306169B2 (en) 2011-03-28 2016-04-05 Sumitomo Chemical Company, Limited Electronic device, polymer compound, organic compound, and method of producing polymer compound

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